


Relationships and Sex

by killypool



Series: Wade Wilson [2]
Category: Deadpool - All Media Types
Genre: F/M, M/M
Language: English
Status: In-Progress
Published: 2019-04-19
Updated: 2019-04-19
Packaged: 2020-01-16 07:55:17
Rating: Not Rated
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 4
Words: 5,189
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/18517183
Author URL: https://archiveofourown.org/users/killypool/pseuds/killypool
Summary: various headcanons regarding Wade Wilson and relationships and sex





	1. Shipping in general

**Author's Note:**

> These headcanons - and everything in this series - are specific to my portrayal of Deadpool. Everyone's allowed their own opinions of the guy and the franchise, but I write him over on killypool.tumblr.com, so this is just for me to have everything nice and neat and organized.

wade is willing to let himself be vulnerable in front of people he genuinely loves and trusts. he’s not afraid to look weak, but rather, he doesn’t want to put the burden of worrying about him on anyone else’s shoulders. he won’t tell people about witness protection, about his mother’s cancer, his father’s abuse, his time in the military, his cancer, his torture, any of that unless they break him down enough to do so. people may get snippets, but you have a better chance of finding out about his past from someone else.

but if he makes himself vulnerable, if he tells you his past, he needs you. he genuinely and truly needs you. he wants you to help him. the things he’s telling you, he’s telling you so that you can better help him when he needs it. he doesn’t need your help all the time, and goddamnit, he’ll find some way to make it up to you for pulling you into his pile of shit, but he needs your help.

and if he tells you the truth and makes himself vulnerable and then comes to you and pleads for you to help him, when he’s close to tears and there’s no joking in his voice and he’s shaking - and god, he’ll shake. he’ll look like the biggest mess you’ve ever seen, because when wade breaks, he shatters. if he comes to you like this and you dismiss him or ignore him or treat it like a joke, you’ve lost him forever because you made him lose another piece of himself that he’s never getting back. he’ll come back to you, he’ll act like nothing’s changed once he finally pulls himself together again, but he won’t be the same person. and he’ll never let himself break down in front of you again. you’ve lost all right to help him. you’ve lost all right to be close to him.

the closest he came to these pleas for help in the movies were going to “mr. smith” in ajax’s workshop for a cure and asking colossus for help saving russel - to which colossus ended up coming and only reaffirming and strengthening wade’s trust in him.


	2. Wade and Vanessa

**Notes for the Chapter:**

> These headcanons - and everything in this series - are specific to my portrayal of Deadpool. Everyone's allowed their own opinions of the guy and the franchise, but I write him over on killypool.tumblr.com, so this is just for me to have everything nice and neat and organized.

wade didn’t exactly have a type before vanessa. he had a few guys that he fooled around with, one or two that he ‘dated’ in high school (without ever really going out on dates). he certainly wasn’t a virgin. he had his fair share of one night stands and flings. none of them followed a set type except wade always found himself in situations where he could help the person he was with. 

broken down on the side of the road, no umbrella on a rainy night, guys leering them at the bar, etc. he always found himself with damsels in distress (or close enough). 

but vanessa? she didn’t need wade for anything. and he liked it. 

it was horrifying. it was scary and new and surprising but wade wasn’t sure what he could do in a relationship with someone who didn’t need him. until he started to realize it was because she wanted him. without him, her life would keep going. but he could make it better. he could make her happier. he wasn’t her hero, and that was the best case scenario. 

some of his best relationships will be with people who will never need him, and only want him. it’ll be rough. he’ll always be searching for a way to ‘earn’ his place beside someone else, but it’ll work out in the end.


	3. Sex, sex, and more sex

**Notes for the Chapter:**

> These headcanons - and everything in this series - are specific to my portrayal of Deadpool. Everyone's allowed their own opinions of the guy and the franchise, but I write him over on killypool.tumblr.com, so this is just for me to have everything nice and neat and organized.

let the record show that wade is extremely talented down under. he’s creative, thorough, willing to keep working even as his jaw grows more and more sore. he’s fantastic, and the good little boy knows exactly where his mouth should be in bed. but when it comes to receiving? poor guy gets oversensitized. it doesn’t take more than a couple of minutes of anyone’s mouth on his cock before he’s warning them he’s about to blow. stamina flies out the window as soon as he looks down and sees someone’s eyes lock with his. 

\--

banter. nothing is sexier than someone matching him in a battle of wits. the best thing for him is to be able to fall into bed with someone he can laugh with because that takes the majority of any insecurities away. finish too quickly? laugh it off and tell them they’re too powerful. fall during sex? dramatically clutch his heart and cry out that he’s wounded. the more someone plays along with him, the more endeared he is to them, though there’s also a strong desire to take someone serious and get them to ease up.

his preferences vary widely, never preferring certain physical traits for very long. one day he’ll prefer blondes, the next he’ll prefer tall men. there’s little physically that he doesn’t find attractive. as for kinks? yelling turns him on. watching someone get frustrated and yelling - ONLY if he isn’t afraid of them hurting him - has him wanting to be put in his place.

\--

wade’s preferred spank bank material? dirty messages. throughout high school, he had a handful of girlfriends and a boyfriend that he would write inappropriate letters with during the school day. many of these letters were saved and taken with him to tide him over. videos and pictures are hot, but thinking about talking out with someone what you want to do knowing that they’re going to be touching themselves thinking of the exact same conversation? unbelievably hot. a relationship with wade guarantees texts throughout the day with every random sex thought that comes to mind.

\--

wade is extremely big on aftercare. even with complete strangers, even with vanilla sex, aftercare is a biggie. cuddling is a mandate if you want to sleep with him because he needs that intimacy. even with one night stands, he wants to believe that he’s worth more than sex and he would never want anyone else to think that all they are is good for sex. he has no qualms about sleeping with strangers, but at the end of the day, he wants to honor that connection they shared with even a few minutes of holding and lazy kissing and catching their breath.

if he’s involved in something intense or anything that involves pain or degradation or even discomfort, wade needs aftercare otherwise he’ll break down. if he was left abandoned or alone after a bdsm scene, he’d be shaken up for days after. even during scenes, he’ll ask for a breather just for someone to kiss his forehead and call him a good boy and remind him they love him before he’s able to continue, but he would only ask if it was someone he was extremely close with.

\--

call him a good boy. call him baby boy. call him babydoll. call him anything sweet, no matter what. princess, babygirl, love, dear, darling. anything and he’ll melt. he needs endearments like that more than he needs air (technically, it’s true). he won’t ask you to say or call him anything, but you’ll be able to watch him light up when you do.

\--

he’s certainly not inexperienced. he has far more experience with girls, the majority of hook ups with men ending up fondling or oral. he hasn’t had very many long term relationships at all, so the majority of his experience is in more vanilla sex because he hasn’t had opportunities to try out anything with a partner he trusts. but he does read and watch enough porn to have the general idea on most acts and will usually look up and research something as soon as he hears about it.

\--

wade is always in the mood. his sex drive is crazy high, though he’ll reach for the crocs and jergens before he goes for a one night stand, and that goes triply so after the mutation. his sex drive is actually even higher then, though there’s very few people he’d trust to have sex with when his skin resembles a dried out asshole. his stamina and refractory period are both pretty fantastic. but wade’s also good about reigning himself in. he doesn’t need to have sex all the time to be in a relationship, and if his sex drive is higher than his partners, he’ll spend more time in the shower every morning and not push it. it’s not a big deal to him.

\--

wade has praise kinks out the ass. he’ll praise you, he wants to be praised. if dirty talking in sex isn’t 75% complimenting how great the other person is, what’s the actual point? he’ll tell you every single thing you do that he likes and he’d love it if you did the same. more than once he’s gotten off by rubbing his hips against the bed while going down on them if they moan and say things like ‘right there, baby, god you make me feel so good.’ BAM. it’s over. he’s too weak for it. 

\--

wade in bed is something else. he’s almost always submissive, though he keeps a mouth. he has something to say about EVERYTHING so please take it as a challenge to get him to shut up. he responds best to being called a good boy or being praised. he wants the other person to be completely pleasured and usually puts them and their pleasure before him and his. he feels most comfortable in bed with someone he can laugh with. sense of humor is legitimately one of the sexiest things to him -especially someone who can match his wit. he’s capable of taking the lead and being more dominant, but in those cases, he remains extremely gentle. it’s incredibly hard for him to be rough to someone during sex - he doesn’t pull hair, choke, spank, etc and would need to work his way up that if he was asked. however, he’s absolutely fine with being treated any way during sex as long as he can always check in and make them stop if it’s too much - and it can get to be too much VERY easily.

\--

wade literally only wants a relationship and a family. sure, families scare him and the idea of raising a child is terrifying but wade will literally be at his maximum happiness if he lived as a stay at home dad with children and maybe a few corgis. Let!! Him!! Be!! A!! Trophy!! Husband!! the boy just wants to wear aprons and literally only aprons as he makes cupcakes for his significant other and then begs to be fucked over the countertop and the fact that he isn’t getting this is the biggest shame

\--

wade will always joke about having a small dick or being super bad in bed (or joke about having a 22inch dick and being a god in bed but he’s very clearly exaggerating). in actuality, his dick is a bit bigger than average (7.5 or so but he doesn’t bother measuring) and he’s pretty decent in bed except he loses all self control when someone goes down on him and he’ll finish in a minute. He prefers to be giving rather than receiving. He’s a submissive little shit who can dom every once in awhile but really gets scared to because he never wants to be too bossy or demanding or rough. He wants aftercare even if the play wasn’t rough at all and he needs a ton of aftercare if he doms - he’ll give the same amount of aftercare in return at least.

\--

wade jokes often about having a small dick and being bad in bed. he’ll joke about finishing in 20 seconds, he’ll joke about not being able to get it up. he has no shame in downtalking himself in sexual contexts. and on the other hand, he’ll occasionally make jokes about having a 22 inch penis - all absolutely said in an exaggerated manner. wade doesn’t mind making fun of himself in bed because he doesn’t feel like he needs to prove things in bed. he’s confident in his ability to get a partner off.

he has a particular fondness for being in a submissive position and will usually enjoy being submissive and bottoming. he likes being able to trust the other person and put his pleasure ( and every so often, his safety ) into his partner’s hands. when he’s the more dominant role, he’s always a gentle dominant and does not want to hurt anyone. it’s a hard pass on him being the one to inflict impact play or blood play, etc. he also doesn’t want to be very bossy or demanding and will frequently check in.

regardless of how vanilla the sex was or whether he was a submissive or dominant, wade needs aftercare after. even if it’s just laying in bed together, he needs a few moments of winding down and kissing and resting after sex to avoid feeling uncomfortable ( used, worthless, good for only sex, etc. ) when he’s dominant, he needs a ton of aftercare after - even if it’s just someone holding him for five minutes and reminding him that he’s not a bad person. he’ll be more than happy to give the same treatment in return.

\--

you would be LUCKY to have wade as a top unless you’re just completely and totally turned off by the concept of fun, laughing, body worshipping sex. wade as a top/dom means that wade is going to spend extra time on every single kind of foreplay, and if you catch him in a particularly teasing mood, him holding you in his lap and telling you how to touch yourself. he’s going to kiss every inch of your body, he’s going to smile and laugh and kiss you and make you feel relaxed. he’s going to rub your shoulders and back while you’re laying in bed together because sometimes positions get weird and he knows the way he bent your over the bed to drill into you wasn’t comfortable. you’re going to leave his bed with kisses pressed to every inch of your skin after having as many orgasms as your body is capable of having and you’re going to like it.

\--

wade is completely fine with things being rough in the bedroom so long as he’s the one getting hurt as opposed to him hurting his partner. while he prefers making love, sometimes he just needs rough sex to put him in the right mindset or clear his mind or just relax him. and when he and his partner both agree to engage in rough play ( consent kids, they always have to both agree ) something very specific will take place.

wade will take as little preparation possible, stretching wise. why? he’s survived being torn in half, it’s really not the most painful thing he’s been through and he adapts quick. but the healing factor? if he’s stretched suddenly, there will be tearing - an injury. a wound that his body tries to heal. as opposed to being stretched slowly without any significant tearing taking place, being stretched suddenly will result in wade’s body trying to heal itself, causing him to become tighter and tighter. this pain for wade is completely negligible, though he does need aftercare after. 

all in all, healing factor + rough anal = one of the most incredible topping experiences anyone will ever experience ever, sorry i don’t make the rules

\--

the first time you have sex with wade after his mutation, regardless of if he’s bottoming or topping ( he’ll usually only top for girls/anyone who doesn’t have a strap on handy ) he is absolutely going to pick a position that makes it impossible to see his face because he can’t imagine how anyone would stay turned on while looking at him. lights off, under the covers, clothes on when possible, doggy style is just his default.

 

\--

wade has a super high sex drive, and after a ton of (protected!) hookups in the army, he realized pretty quick that he’d rather have longer lasting relationships. because he never really had long relationships, his right hand became his best friend. and his left. gotta switch it up. he’ll joke about it but seriously he will get pouty and grumpy if he can’t indulge every night - exceptions only being for when he’s in unbearable pain (being tortured, with the collar on). normal chronic pain isn’t enough to stop him from pulling out the Jergen’s.

in fact, even when in a committed relationship, he’s still gonna yank it because it’s just habit. it doesn’t bother him when his partner has a low sex drive or no sex drive, though he’ll take WAY longer baths. but when his partner has the same sex drive he does? you’re not gonna see him for a year, bye. wade’s honeymoon stages last for years.

\--

he was 16 the first time he slept with someone. he had snuck out of his group home to attend a party and was drawn in by the mediocre basement lighting and unchilled pabst blue ribbon. it was a girl that he was already close to dating, though wade didn’t exactly do the whole ‘dating’ thing. they snuck upstairs to a friend’s bedroom and - in a moment of panic - snuck into the friend’s parents bedroom in hopes of finding protection. safety first, kiddos. her name was marissa hegranes and after their tryst, they lasted a whole three months of staring at each other in geometry and making out at each other’s lockers.

\--

the first time a girl ever broke wade’s heart was when he was in the military. he had only slept with one other girl - janice smith, junior year of high school - when he met stacy richards during his deployment. she was funny and gorgeous and strong willed and talked with him every chance she got. after three months of build up, he finally spent a night with her. what he didn’t expect was for her to kick him out of bed as soon as they finished telling him to ‘not mention it again.’ it took wade way too many times to figure out that going straight to sleeping with someone usually ended with an orgasm. it was the most effective in making him realize never to assume anyone ever wanted you for longer than you were useful.

\--

on the surface, wade will give anyone a shot. anyone who shows enough interest in him is a potential partner. but to have a long lasting relationship with wade, you have to be patient. you need the patience to realize that his humor is a defense. you need to be patient enough to work with him instead of trying immediately to change him. if you go in treating him like a fixer - upper project, you’ve lost him. he’s not going to change for you if you’re changing him to be able to tolerate him. he won’t deal with abuse or with neglect or with abandonment. he’ll lose interest if you don’t have a sense of humor. but in general? if you ever make him feel like he’s not wanted, he’ll be out the door before you can say goodbye.

\--

wade’s absolutely slept with his fair share of people. before he meets vanessa, he’s 38 years old and had never really had a serious, long term relationship. he slept with two girls in high school, and at least a couple dozen men and women during his combined 15 years in the military. after his dishonorable discharge, hookups really weren’t a priority. he slept with the odd one night stand during particularly weak moments, but he’d grown mostly disillusioned with the idea of a relationship starting. all in all? he’s probably over 50, all things considered. and while wade regularly engages in risky behavior, every single encounter was with protection and he’s had regular-ish std tests. he doesn’t care about his own health very much, but he would never risk fucking up someone else’s life just because he didn’t feel like wrapping it up.

\--

one of the most important rules of hooking up? besides wrapping it up and staying safe? stay vanilla. don’t pull out the paddles or cuffs for any average joe off the street. if you want to get bdsm-y, save it for someone you trust. one of the worst experiences wade had was a girl who wanted to be degraded, begged him to insult her and grab her roughly, and he did - for the most part. and he had fun - mostly. but when all was said and done, she hopped right back up once they were done and said her goodbyes, leaving wade alone in his apartment without aftercare – why should it matter? it’s not like the dominant needs aftercare too. – and left him feeling like a monster for hours after. the feeling lingered for days, and he’s still hesitant to be anything more than a gentle dom.

\--

wade is hypersexual, and this may be mostly attributed to his own history as a csa survivor. it's what he knows and it's what he thinks he's good for. in any case where he has sex before a relationship is established, he's already assuming it's going to go south, and he's planning on them never wanting to see him again. sex can absolutely be a form of self harm for wade.

\--

wade automatically assumes with any of his (numerous) one night stands that they don’t want him for longer than a night because that’s what experience told him. It’s why he’ll genuinely try to take at least some time before sleeping with someone he cares about. Sometimes that only ends up being another hour or two, but still. 

If he’s having sex with someone and he feels like they are just using him for sex - if they’re too rough, too demanding, too degrading - a switch is turned on in his head. Not quite subspace, because he’s usually submissive in general but wade is smart enough to know never to be submissive when someone is already using him. No, not quite a subspace, but he enters a headspace where he isn’t gentle either. He’ll let himself be selfish because he might as well. He knows (thinks) his partner doesn’t value him but any chance to feel close to someone for a moment is needed, no matter how unhealthy.

And if it’s someone he cares about? If he feels like someone he genuinely cares for is using him for sex? He’ll avoid them whenever possible. He’ll be shorter with them, less talkative. But if he’s ever inebriated, they’re gonna get long ass texts about how “it’s okay you only want to fuck me. That makes sense. Can’t blame you. Since that’s all you want, come get it.” And it’s manipulative and hurtful, but he feels like he’s just being truthful.

\--

no one asked for this but wade in the bedroom is literally so eager to please that someone could pull a knife out and he’d agree immediately (even though halfway through he might change his mind and not say anything because he’s not prepared for someone to be mad at him for wanting to stop) but at the same time, he feels uncomfortable with himself being rough. he could grip someone’s hips so hard they bruise or he could scratch someone’s back while they’re fucking him, but besides that? he’s too terrified of hurting someone. but at the same time he’d let himself be literally torn in half. he tries not to be overly submissive with people he’s total strangers with out of fear but if he already respects/admires you and you’re having sex and he doesn’t feel confident enough to speak up, he’d let his partner do anything.

\--

wade doesn’t discriminate when it comes to location. a tendency for recklessness means he’d be game for anywhere in public that isn’t around children. but besides that? alleyways, the showers at the gym, the backs of cars, etc. but the older he gets, the more he has a preference for just staying in bed. variety is the spice of life, but sometimes just loving, tender sex under the covers on sunday morning is just what the proctologist ordered.

\--

if he’s in a relationship with someone, he would at one point have a conversation about whether or not it’s okay to wake his partner up with oral. and if he gets enthusiastic consent, one of his favorite things is covering his partner in kisses before they ever open their eyes. the idea of getting someone off in their sleep is ridiculously hot to him also, and would definitely be something he’d ask to try. as for the other way around? well, he can’t possibly think of a better way to wake up.

\--

the man is an intimate fool. if he’s with someone he cares about, he’s talkative and he’s loving and there’s a ton of eye contact and kisses and holding onto each other. he’s very open about his feelings once he’s sure his partner feels the same or won’t run away, and he won’t hold back on the sappy love confessions in bed. most of his enjoyment comes from making sure his partner is enjoying it, after all.

\--

his pace depends entirely on his partner. if his partner is energetic, he’ll be high energy. if his partner wants to slow down, he’ll slow down. when he initiates, he tends to gravitate towards a high intensity but average pace. he doesn’t deliberately want to rush things - he craves intimacy with a partner too much to get it over as soon as possible. regardless of how it goes, he’s going to be up for another round. and then another round. and then another. over and over until his partner can’t go any more.

\--

wade isn’t always too big on being tied up in the bedroom, but if he wants to be good (and you give him motivation to be good) he will lie very still on the bed no matter what. Even if you to something to torture him like use a wand on his cock and edge him and overstimulate him for hours. 9/10 he will lay there very obediently. (Unless the punishment for being bad is better than the reward for being good)

\--

costumes are all fun and games - especially during the merry month of october - but who could prefer them to lingerie? costumes are a treat - a bit of roleplay, a nurse’s costume or a firefighter costume or a schoolgirl costume. it spices up the bedroom. but lingerie is art. and art can’t get overused. wade would be more than happy to wear lace panties in favor of boxers or briefs every day. and if his partner was wearing dangerous black or red silk or lace or leather beneath their unassuming clothes? even. fucking. hotter.

\--

Wade’s sex drive is through the roof always, so he’s usually down with one night stands assuming his skin looks normal. But regardless of whether or not he’s hooking up, he masturbates all the time. An insane amount. He’ll chill out on the self love when he’s with a partner, but if he’s alone, it’s no holds barred. So word of advice for anyone who wants to walk into Wade’s room or apartment or hotel room without earning - KNOCK. (Unless you want a show. Because he’s an annoying fuck who’d gladly give you one.)

\--

one of wade’s most FAVORITE things is making someone laugh while they’re having sex and while they’re laughing, do something that makes that laugh turn into a gasp or a moan or a scream. the transition of careless laughter to desperate moaning is one of the most beautiful sounds and you can’t change wade’s mind on that.


	4. Wade in relationships

**Notes for the Chapter:**

> These headcanons - and everything in this series - are specific to my portrayal of Deadpool. Everyone's allowed their own opinions of the guy and the franchise, but I write him over on killypool.tumblr.com, so this is just for me to have everything nice and neat and organized.

wade isn’t exactly clingy. he won’t demand to always know where you are if you’re dating. he won’t be jealous. he won’t demand attention or force you to stay with him if you ever even give him the idea you don’t want him. but he’ll make it clear how much he loves you. he’ll pull you close every night and kiss you and he’ll be the first to say ‘i love you.’ because life is too shitty to not let people know you love them as soon as you’re sure you do. he’s not clingy but he might be the more affectionate in the relationship. he’ll be more open about how much he loves you and wants you and needs you because he’ll never be ashamed of who he loves. if he’s too affectionate or too loving and it’s too much (because it can be too much) and you push him away or tell him to stop, he’ll agree and do whatever you say, but it will break his heart. any small rejection breaks his heart, but wade isn’t in the habit of trying to keep his heart safe.

\--

wade wants to be a dad and take his family to Disney world. He wants to have barbecues. He wants to go trick or treating and spend hours making the costumes. He’s gonna deck the cashier at a toy store if they tell him that his son needs a manly toy or his daughter needs a girl’s toy. He wants tea parties and making soapbox cars and flying kites and being there for his kids for everything because wade will drop everything for them.

\--

wade has absolutely lied about himself when he was flirting with a girl or a guy but instead of making himself seem cooler than he is, he tries to make himself seem way lamer. “oh yeah, I’m a pizza boy by trade. grew up on a mozzarella farm. I want to name my son basil.” and he gets the person to go home with him because he’s charming and hey his green beret fatigues are hanging up in the corner and this dorky guy is ridiculously badass.

\--

he’ll find stupid excuses to stay in someone’s bed if given the opportunity. baby it’s cold outside. burglars in the neighborhood. sudden and debilitating leg cramps. even if he can’t stay for more than a couple of hours, he needs that tiny reassurance that he still means something. as much as he’s ready to let people use him, he’s terrified of it once it actually happens.

\--

**how young of a partner would wade settle for in a relationship? :o**

It depends on Wade’s own age at the time. In his main timeline post DP 2, he’s 42. At 42, younger than 27 would give him serious pause. Pre Deadpool when he’s 37/38, he wouldn’t really date younger than 25.

I do have a verse where Wade became Deadpool earlier - he was injured during his time in the military and taken to a “hospital” that ended up being the workshop. There, he’d be around 30, and he’d date 21+.

Of course, exceptions can be made, but Wade isn’t going to pursue anyone himself if the person in question is early 20s.

\--

wade lets himself get injured during all fights to throw off his opponent, but when fighting off attackers in his apartment, he was careful not to get injured so vanessa wouldn’t see him hurt

\--

 


End file.
